Patent GB-554601-A (GB)
Title: New monoazo dyestuffs
IPC: C09B29/30
Filed: 1941-10-08
Abstract: 554,601. Dyes. KNIGHT, A. H., STEPHEN W. E., and IMPERIAL CHEMICAL INDUSTRIES, Ltd., Oct. 8, 1941, Nos 12981 and 12982. [Class 2 (iii)] Monoazo dyes are obtained by diazotizing an amine of the formula X-CO-NY-R-NH 2 , wherein X represents a monochloro- or monobromo-alkyl radicle having not more than 3 carbon atoms, R represents a benzene residue, .which may be substituted, Y represents hydrogen, unsulphonated alkyl (C 1  to C 6 ), aralkyl, - cycloalkyl, alkoxyalkyl or aryl,-the NY group being in m- or pposition to the primary amino group, and coupling with an N - acyl - 2:5:7- aminonaphtholsulphonic acid in which the acyl group is formyl, alkoxyformyl, succinyl, benzoyl, substituted benzoyl, arylsulphonyl, hydroaromatic sulphonyl, hydroarpmatic carbonyl or of the type -CO-(CnH 2 n)-O-B, wherein n represents 1, 2 or 3 and B represents alkyl (C 1  to C 4 ), aryl, cycloalkyl or aralkyl, and the coupling component may be further N - substituted by alkyl or aryl. Specified diazo components are the 4 - amino - 1 - N - ethyl, isopropyl, n - butyl, sec.-butyl, benzyl, cyclohexyl and phenyl derivatives of chloroacetanilide,. the 4 - amino - N - ethyl and benzyl derivatives of 2 - chloracettoluidide, the 4 - amino - N - ethyl derivatives of 2 - α - and # - bromopropiontoluidides, 3 - amino - chloroacetanilide or # - chloropropinnanilide - 4 - sulphonic acid, 2 - amino 4 - N-ethyl - chloroacettoluidide, 4 - amino - 2 - N - ethyl - α - bromobutyryltoluidine, 4 - amino - 2 - N ethyl- # - chloropropiontoluidide, 4 - amino - 1 - N - ethyl - # - chloro - or bromo-propionanilide, 4 - amino - chloracetanilide - 3 - sulphonic acid, the 4 - amino - N - ethyl and benzyl derivatives of 2 - chloroacetanisidide, 4 - amino - 1 - N - n - butyl - chloroacetanilide - 2 - sulphonic acid, 4 - amino - 1 - N - ethyl - bromacetanilide, 5 - amino - 2 - N - cyclohexyl - chloracettoluidide, 3 - amino - 1 - N - benzyl - chloroacetanilide, the 4 - amino - 1 - N - cyclohexyl derivatives of bromoacetanilide, α - and #- bromopropionanilides and # - chloroprdpionanilide and 4 - amino - 1 - N - # - ethoxyethyl - chloroacetanilide. Specified N-substituents in the coupling components are formyl, N-phenylformyl, ethoxy-formyl, succinyl, N - ethyl - succinyl, benzoyl, N - ethyl benzoyl, 2<SP>1</SP> - chlorobenzoyl, N - ethyl - 2<SP>1</SP> - chlorobenzoyl, 3<SP>1</SP> - bromobenzoyl, benzenesulphonyl, p - toluenesulphonyl, N - methyl - or ethyl - p - toluenesulphonyl, tetrahydronaphthalene - 2'- sulphonyl, hexahydrobenzoyl, methoxy-, ethoxy-, or n - butoxyacetyl, N - ethyl - or phenyl-methoxyacetyl, phenoxy-acetyl, 2<SP>1</SP>- or 4<SP>1</SP>- chloro-phenoxyacetyl, 4<SP>1</SP>- methylphenoxyacetyl, N - ethyl - phenoxyacetyl, N - ethyl- 21 - chlorophenoxyacetyl, # - phenoxypropionyl,cyclohexyloxyacetyl and benzyloxyacetyl The products are applicable for the production of orange dyeings on animal fibres, e.g. wool and silk, the dyeings on wool from an acid bath being very fast to severe washing and milling and fast to light. Examples relate to the production of the dyestuffs, (1) 4 - amino - 1 - N - ethyl - chloroacetanilide # N - methoxyacetyl - 2:5:7- acid ; (2) 4 - amino - 2 - N - ethyl - chloroacettoluidide # N - methoxyacetyl - 2:5:7- acid ; (3) 4 - amino - 1 - N - cyclohexyl - chloroacetanilide # N - methoxy-, ethoxy- or nbutoxy-acetyl - 2:5:7 - acid ; (4) 4 - amino - 2 - N - ethyl - chloroacettoluidide or 4 - amino - 1 - N - isopropyl - chloroacetanilide # N - (21- chlorophenoxyacetyl) - 2 : 5 : 7 - acid ; (5) 4 - amino chloroacetanilide - 3 - sulphonic acid# N - methoxyacetyl - 2:5:7 - acid ; (6) 4 - amino- 2 - N - ethyl- α or #- bromo- or #- chloropropiontoluidide # N - phenoxyacetyl - 2:5:7- acid ; (7) 4 - amino - 1 - N - # - ethoxyethyl - chloroacetanilide # N - methoxyacetyl - 2:5:7- acid ; (8) 4 - amino - 1 - N - isopropyl - chloroacetanilide # N - benzyloxyacetyl - 2:5:7 - acid; (9) 4 - amino - 1 - N - ethyl - chloroacetanilide # N - benzoyl - 2:5:7 - acid; (10) 4 - amino - 2 - N - ethyl - chloroacettoluidide # N - ethyl - benzoyl - 2:5:7 - acid ; (11) 4 - amino - 1 - N - ethyl - # - chloro- or bromo-propionanilide # N - (p - toluenesulphonyl)- 2:5:7 - acid ; (12) 4 - amino - 1 N - cyclohexyl - chloroacetanilide # N- ethoxyformyl - benzenesulphonyl or p - toluenesulphonyl - 2 : 5 : 7 - acid; (13) 4 - amino - 1 - N - cyclohexyl - chloroacetanilide # N - succinyl- or benzoyl - 2:5:7 - acid ; (14) 3 - amino - 1 - N - benzyl - chloroacetanilide # N - methyl - or ethylp - toluenesulphonyl- 2:5:7-acid ; (15) 4 - amino - 1 - N - n - butyl - chloroacetanilide - 2 - sulphonic acid # N - formyl - 2:5:7 - acid A table is also given showing the shades obtainable on wool with the dyestuffs from various other combinations of components. Specifications 424,354, 472,171, 544,409 and 553,204 are referred to. N - formyl - 2:5:7 acid and its N - alkyl and N - aryl derivatives are obtained by the action of an excess of formic acid on 2:5:7 - aminonaphtholsulphonic acid and its N - alkyl and N - aryl derivatives. N-succinyl-, N-benzoyl- N-benzenesulphonyl-, N-p-toluenesulphonyl-, N-tetrahydronaphthalene- 2-sulphonyl-and N-hexahydrobenzoyl-derivatives of 2:5:7 - acid are obtained by the action, in presence of an acid-binding agent, of succinic anhydride, benzoyl chloride, benzenesulphonyl chloride, p - toluenesulphonyl chloride, tetrahydronaphthalene - 2 - sulphonyl chloride and hexahydrobenzoyl chloride respectively on 2:5:7 - aminonaphtholsulphonic acid. N - alkoxyacyl derivatives of 2:5:7 - acid and of its N - alkyl and N - aryl derivatives are obtained by the action of the chloride or anhydride of the appropriate alkoxy-substituted fatty acid on 2:5:7-aminonaphtholsulphonic and its N - alkyl - and N- aryl derivatives. N - aryloxy -, N - cycloalkoxy and N - aralkoxy - acyl derivatives of 2:5:7 - acid and its N - alkyl derivatives are obtained by the action of the appropriate N - aryloxy -, N - cycloalkoxy- and N - aralkoxy-acyl chlorides on 2:5:7 - aminonaphtholsulphonic acid and its N - alkyl derivatives.